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Synlett 1990; 1990(9): 501-503
DOI: 10.1055/s-1990-21141
DOI: 10.1055/s-1990-21141
letter
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Stereocontrolled Access to all-trans α,β,γ-Substituted Pyrrolidinones and Pyrrolidines of High Optical Purity from D-Pyroglutamic Acid
Further Information
Publication History
Publication Date:
08 March 2002 (online)
A procedure was developed for the stereocontrolled conjugate addition of dialkyllithiocuprates to an α,β-unsaturated lactam (3-phenyl-1H,3H-pyrrolo[1,2-c] oxazol-5(7a)-one) derived from D-pyroglutamic acid (D-2-pyrrolidone-5-carboxylic acid). Formation of the corresponding enolates and treatment with alkyl halides, aldehydes or acetone gave α,β,γ-substituted pyrrolidinones and pyrrolidines of high optical purity.